Synonym
Nicergoline, Nicotergoline, Nimergoline, Sermion
IUPAC/Chemical Name
[(6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinoline-9-yl]methyl 5-bromopyridine-3-carboxylate
InChi Key
YSEXMKHXIOCEJA-FVFQAYNVSA-N
InChi Code
InChI=1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1
SMILES Code
O=C(C1=CC(Br)=CN=C1)OC[C@H](C[C@]23OC)CN(C)[C@]3([H])CC4=CN(C)C5=C4C2=CC=C5
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Nicergoline is a potent, selective and orally active antagonist of α1A-adrenoceptor.
In vitro activity:
In microglia stimulated with LPS and IFN-gamma, nicergoline suppressed the production of superoxide anions, interleukin (IL)-1beta, IL-6, and tumor necrosis factor (TNF)-alpha in a dose-dependent manner. In astrocytes, nicergoline also suppressed the production of proinflammatory cytokines and enhanced brain-derived neurotrophic factor (BDNF).
Reference: Brain Res. 2005 Dec 20;1066(1-2):78-85. https://pubmed.ncbi.nlm.nih.gov/16325157/
In vivo activity:
The results of the present study demonstrated that nicergoline ameliorated apoptosis in hippocampal cells and hippocampus tissue in 3xTg‑AD mice with Alzheimer's disease. The data indicated that apoptosis‑associated genes, including caspase‑3, BCL2 associated X, BH3 interacting domain death agonist and caspase‑9, were downregulated in hippocampal cells isolated from nicergoline-treated experimental mice. Additionally, amyloid precursor protein accumulation was cleared in the hippocampal area in nicergoline‑treated mice. Nicergoline inhibited neuronal loss and prevented cognitive impairment through the restoration of learning/memory ability.
Reference: Mol Med Rep. 2018 May;17(5):7293-7300. https://pubmed.ncbi.nlm.nih.gov/29568940/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
20.0 |
41.29 |
|
| DMSO |
47.3 |
97.72 |
|
| DMSO:PBS (pH 7.2) (1:9) |
0.1 |
0.21 |
|
| Ethanol |
10.0 |
20.64 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
484.39
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Mizuno T, Kuno R, Nitta A, Nabeshima T, Zhang G, Kawanokuchi J, Wang J, Jin S, Takeuchi H, Suzumura A. Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes. Brain Res. 2005 Dec 20;1066(1-2):78-85. doi: 10.1016/j.brainres.2005.10.050. Epub 2005 Dec 1. PMID: 16325157.
2. Caraci F, Chisari M, Frasca G, Canonico PL, Battaglia A, Calafiore M, Battaglia G, Bosco P, Nicoletti F, Copani A, Sortino MA. Nicergoline, a drug used for age-dependent cognitive impairment, protects cultured neurons against beta-amyloid toxicity. Brain Res. 2005 Jun 14;1047(1):30-7. doi: 10.1016/j.brainres.2005.04.004. PMID: 15882840.
3. Zang G, Fang L, Chen L, Wang C. Ameliorative effect of nicergoline on cognitive function through the PI3K/AKT signaling pathway in mouse models of Alzheimer's disease. Mol Med Rep. 2018 May;17(5):7293-7300. doi: 10.3892/mmr.2018.8786. Epub 2018 Mar 20. PMID: 29568940.
4. Alvarez-Guerra M, Bertholom N, Garay RP. Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol. 1999;13(1):50-8. doi: 10.1111/j.1472-8206.1999.tb00320.x. PMID: 10027088.
In vitro protocol:
1. Mizuno T, Kuno R, Nitta A, Nabeshima T, Zhang G, Kawanokuchi J, Wang J, Jin S, Takeuchi H, Suzumura A. Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes. Brain Res. 2005 Dec 20;1066(1-2):78-85. doi: 10.1016/j.brainres.2005.10.050. Epub 2005 Dec 1. PMID: 16325157.
2. Caraci F, Chisari M, Frasca G, Canonico PL, Battaglia A, Calafiore M, Battaglia G, Bosco P, Nicoletti F, Copani A, Sortino MA. Nicergoline, a drug used for age-dependent cognitive impairment, protects cultured neurons against beta-amyloid toxicity. Brain Res. 2005 Jun 14;1047(1):30-7. doi: 10.1016/j.brainres.2005.04.004. PMID: 15882840.
In vivo protocol:
1. Zang G, Fang L, Chen L, Wang C. Ameliorative effect of nicergoline on cognitive function through the PI3K/AKT signaling pathway in mouse models of Alzheimer's disease. Mol Med Rep. 2018 May;17(5):7293-7300. doi: 10.3892/mmr.2018.8786. Epub 2018 Mar 20. PMID: 29568940.
2. Alvarez-Guerra M, Bertholom N, Garay RP. Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol. 1999;13(1):50-8. doi: 10.1111/j.1472-8206.1999.tb00320.x. PMID: 10027088.
1: Zajdel P, Bednarski M, Sapa J, Nowak G. Ergotamine and nicergoline - facts and myths. Pharmacol Rep. 2015 Apr;67(2):360-3. doi: 10.1016/j.pharep.2014.10.010. Epub 2014 Oct 30. Review. PubMed PMID: 25712664.
2: Fioravanti M, Nakashima T, Xu J, Garg A. A systematic review and meta-analysis assessing adverse event profile and tolerability of nicergoline. BMJ Open. 2014 Jul 30;4(7):e005090. doi: 10.1136/bmjopen-2014-005090. Review. PubMed PMID: 25079927; PubMed Central PMCID: PMC4120366.
3: Saletu B, Garg A, Shoeb A. Safety of nicergoline as an agent for management of cognitive function disorders. Biomed Res Int. 2014;2014:610103. doi: 10.1155/2014/610103. Epub 2014 Aug 28. Review. PubMed PMID: 25243157; PubMed Central PMCID: PMC4163411.
4: Damulin IV. [Therapeutic potential and possibilities of using of sermion (nicergoline) in neurological practice]. Zh Nevrol Psikhiatr Im S S Korsakova. 2010;110(12):119-22. Review. Russian. PubMed PMID: 21434467.
5: Fioravanti M, Flicker L. Efficacy of nicergoline in dementia and other age associated forms of cognitive impairment. Cochrane Database Syst Rev. 2001;(4):CD003159. Review. PubMed PMID: 11687175.
6: Moretti A, Arcari G, Pegrassi L. [A review of pharmacological studies on nicergoline]. Arzneimittelforschung. 1979;29(8a):1223-7. Review. German. PubMed PMID: 44197.
7: Winblad B, Fioravanti M, Dolezal T, Logina I, Milanov IG, Popescu DC, Solomon A. Therapeutic use of nicergoline. Clin Drug Investig. 2008;28(9):533-52. Review. PubMed PMID: 18666801.
8: Arii T, Katayama Y. [Nicergoline, ibudilast, ifenprodil tartrate]. Nihon Rinsho. 2006 Oct 28;64 Suppl 7:602-5. Review. Japanese. PubMed PMID: 17461212.
9: Fariello RG. Treatment of impaired cognition with nootropic drugs: nicergoline versus the state of the art. Funct Neurol. 1997 May-Aug;12(3-4):221-5. Review. PubMed PMID: 9218984.
10: Moretti A. [Metabolic and neurochemical effects of nicergoline on the central nervous system. A review of the experimental studies (author's transl)]. Arzneimittelforschung. 1979;29(8a):1213-23. Review. German. PubMed PMID: 395953.
